Misplaced Pages

This is an old revision of this page, as edited by Beetstra (talk | contribs) at 20:59, 6 August 2011 (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Quetiapine

Clinical data
Routes of administration	Oral
ATC code	N05AH04 (WHO)
Legal status
Legal status	US: WARNINGRx-only
Pharmacokinetic data
Bioavailability	9%
Metabolism	Hepatic
Elimination half-life	6 hours
Excretion	Renal
Identifiers
IUPAC name 2-(2-(4-dibenzothiazepine- 11-yl- 1-piperazinyl)ethoxy)ethanol
CAS Number	111974-69-7
PubChem CID	5002
IUPHAR/BPS	50
DrugBank	DB01224
ChemSpider	4827
UNII	BGL0JSY5SI
KEGG	D08456
ChEBI	CHEBI:8707
ChEMBL	ChEMBL716
CompTox Dashboard (EPA)	DTXSID9023546
ECHA InfoCard	100.131.193
Chemical and physical data
Formula	C21H25N3O2S
Molar mass	383.5099 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES N\1=C(\c3c(Sc2c/1cccc2)cccc3)N4CCN(CCOCCO)CC4
InChI InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2 Key:URKOMYMAXPYINW-UHFFFAOYSA-N
(verify)

Quetiapine (/kwˈtaɪ.əpiːn/ kwi-TY-ə-peen) (branded as Seroquel, Ketipinor), is an atypical antipsychotic approved for the treatment of schizophrenia, and bipolar disorder.

Annual sales are approximately $5.7 billion worldwide, and $2.9 billion in the United States. The U.S. patent, which was set to expire in 2011, received a pediatric exclusivity extension which pushed its expiration to March 26, 2012. The patent has already expired in Canada. There are now several generic versions of quetiapine, such as Quepin made by Specifar ABEE, Athens, Greece.

Medical uses

Quetiapine is used to treat either schizophrenia or bipolar disorder.

In those with bipolar it is used for depressive episodes, acute manic episodes associated with bipolar I disorder (as either monotherapy or adjunct therapy to lithium or valproate), and maintenance treatment of bipolar I disorder (as adjunct therapy to lithium or divalproex).

It is sometimes used off-label, often as an augmentation agent, to treat conditions such as obsessive-compulsive disorder, post-traumatic stress disorder, restless legs syndrome, autism, alcoholism, depression, Tourette syndrome, and has been used by physicians as a sedative for those with sleep disorders or anxiety disorders.

In 2005, the National Institute of Mental Health examined quetiapine and other antipsychotics to uncover the comparative efficacy of "second generation" anti-psychotics against older anti-psychotics (known as "first generation" or "typical anti-psychotics"). Such information could be important to the patients, as the newer drugs are far more expensive than their older counterparts. Published in the New England Journal of Medicine, the results of the CATIE ("clinical antipsychotic trials of interventional effectiveness") trial were somewhat mixed. 74% of trial participants (of the 1,493 people who were in different treatment groups) discontinued before the trial ended. The majority of the participants discontinued treatment due to intolerable side-effects or lack of efficacy. Olanzapine (Zyprexa) was considered the most effective in terms of the time it took patients to drop out of the study, although it was associated with greater weight gain and glucose intolerability found in diabetes patients. The effects of all other treatments (such as Seroquel) were considered to be similar to the effects of the generic (and dramatically less expensive) drug, perphenazine.

Quetiapine is ineffective in reducing agitation among Alzheimer's patients, whose usage of the drug constituted 29% of sales. In fact, quetiapine was found to worsen cognitive functioning in elderly patients with dementia.

Adverse effects

The most common side-effect of quetiapine is somnolence. Other common side-effects include: sluggishness, fatigue, dry mouth, sore throat, dizziness, abdominal pain, constipation, upset stomach, orthostatic hypotension, inflammation or swelling of the sinuses or pharynx, increased appetite, and weight gain.

It is marketed as one of the most sedating of all anti-psychotics, although those claims are contested. Beginning users may feel extremely tired and 'out of it' for the first few days, and sometimes longer. Quetiapine's newest indication, for bipolar depression, usually specifically calls for the entire dose to be taken before bedtime due to its sedative effects. The sedative effects may disappear after some time on the drug, or with a change of dosage, and with possibly different, non-sedative side-effects emerging.

As with most neuroleptic antipsychotics, the prolonged use of high doses (over 200 mg) of quetiapine increases the risk of the patient developing tardive dyskinesia, an incurable neurological disorder. The risk of suffering tardive dyskinesia becomes greater the longer Seroquel treatment continues, so patients may want to consider alternate options before using Seroquel, especially if in a high-risk category.

The rare, but life-threatening, neuroleptic malignant syndrome may also result from quetiapine use.

Weight gain can be a problem for some patients, as quetiapine causes the patient's appetite to persist even after meals. However, this effect may occur to a lesser degree compared to some other atypical anti-psychotics such as olanzapine or clozapine.

Studies conducted on beagles have resulted in the formation of cataracts. While there are reports of cataracts occurring in humans, controlled studies including thousands of patients have not demonstrated a clear causal association between quetiapine therapy and this side-effect. (Reference needed to April 2006 results of CATIE study.) However, the Seroquel website still recommends users have eye examinations every six months.

As with some other anti-psychotics, quetiapine may lower the seizure threshold, and should be taken with caution in combination with drugs such as bupropion.

A recent comparative study of anti-psychotics drugs has found that quetiapine mono treatment was associated with increased risk of death relative to the other analyzed treatments.

Quetiapine strongly affects the adrenergic system (vasoconstriction) and can therefore cause problems with cerebral blood flow and circulatory system in general.

An occasionally reported side-effect of quetiapine is sleep paralysis possibly accompanied by hypnagogia. The likelihood of this occurrence increases when combined with the intake of alcohol or when the user tries to fight off the sedation caused by larger doses of quetiapine.

Long-term use may cause brain damage or reduce life expectancy - see Antipsychotic#Side effects for details.

Discontinuation

Quetiapine should be discontinued gradually, with careful consideration from the prescribing doctor, to avoid withdrawal symptoms or relapse.

The British National Formulary recommends a gradual withdrawal when discontinuing anti-psychotic treatment to avoid acute withdrawal syndrome or rapid relapse. Due to compensatory changes at dopamine, serotonin, adrenergic and histamine receptor sites in the central nervous system, withdrawal symptoms can occur during abrupt or over-rapid reduction in dosage. Withdrawal symptoms reported to occur after discontinuation of quetiapine include nausea, emesis, lightheadedness, diaphoresis, dyskinesia, orthostasis, tachycardia, nervousness, dizziness, headache, excessive non-stop crying, and anxiety. The present evidence suggests that these symptoms affect a small number of susceptible individuals treated with Quetiapine. Complicated and long-lasting rebound insomnia symptoms can also occur after withdrawing from quetiapine.

Overdosage

Most instances of acute overdosage result only in sedation, hypotension and tachycardia, but cardiac arrythmia, coma and death have occurred in adults. Serum or plasma quetiapine concentrations are usually in the 1–10 mg/L range in overdose survivors, while postmortem blood levels of 10–25 mg/L are generally observed in fatal cases.

Pharmacology

Quetiapine has the following pharmacological actions:

• D₁ (IC₅₀ = 1268nM), D₂ (IC₅₀ = 329nM), D₃, and D₄ receptor antagonist
• 5-HT_1A (IC₅₀ = 717nM), 5-HT_2A, 5-HT_2C, and 5-HT₇ receptor antagonist
• α₁-adrenergic (IC₅₀ = 94nM) and α₂-adrenergic receptor (IC₅₀ = 271nM) antagonist
• H₁ receptor (IC₅₀ = 30nM) antagonist
• mACh receptor (IC₅₀ = >5000nM) antagonist

This means Quetiapine is a dopamine, serotonin, and adrenergic antagonist, and a potent antihistamine with clinically negligible anticholinergic properties. Quetiapine binds strongly to serotonin receptors. Serial PET scans evaluating the D₂ receptor occupancy of quetiapine have demonstrated that quetiapine very rapidly disassociates from the D₂ receptor. Theoretically, this allows for normal physiological surges of dopamine to elicit normal effects in areas such as the nigrostriatal and tuberoinfundibular pathways, thus minimizing the risk of side-effects such as pseudo-parkinsonism as well as elevations in prolactin. Some of the antagonized receptors (serotonin, norepinephrine) are actually autoreceptors whose blockade tends to increase the release of neurotransmitters.

Norquetiapine is the active metabolite of quetiapine. It has most of the effects of quetiapine with similar potencies, and is also a potent norepinephrine reuptake inhibitor and muscarinic antagonist. Note that the data below is from another source (the official prescribing info for Seroquel), and the measure is different from the above (Ki vs. IC₅₀). There are still order-of-magnitude discrepancies for D₁, α₁, H₁ and M₁.

Synthesis

Warawa, E. J.; Migler, B. M.; 1988, U.S. patent 4,879,288.

Dosage

At very low doses quetiapine acts primarily as a histamine receptor blocker (antihistamine) and α₁-adrenergic blocker. When the dose is increased quetiapine activates the adrenergic system and binds strongly to serotonin receptors and autoreceptors. At high doses (over 250 mg) quetiapine starts blocking significant amounts of dopamine receptors. Use of low-dose quetiapine is not recommended except temporarily during drug titration period (less than 30 days).

Due to compensatory changes at dopamine, serotonin, adrenergic and histamine receptor sites in the central nervous system, a gradual reduction in dosage is recommended to minimise or avoid withdrawal symptoms. Withdrawal symptoms reported to occur after discontinuation of quetiapine include: insomnia, nausea, emesis, lightheadedness, diaphoresis, orthostasis, tachycardia, as well as nervousness, dizziness, headache, and anxiety. The present evidence suggests that these symptoms affect a small number of susceptible individuals treated with quetiapine. Chronic and long-lasting (months) rebound insomnia symptoms can occur after discontinuation of quetiapine.

The British National Formulary recommends a gradual withdrawal when discontinuing antipsychotic treatment to avoid acute withdrawal syndrome or rapid relapse.

Sustained-release

AstraZeneca submitted a new drug application for a sustained-release version of quetiapine in the United States, Canada, and the European Union in the second half of 2006 for treatment of schizophrenia. AstraZeneca will retain the exclusive right to market sustained release quetiapine until 2017. The sustained-release quetiapine is marketed mainly as Seroquel XR. Other marketing names are Seroquel Prolong and Seroquel Depot.

On May 18, 2007, AstraZeneca announced that the FDA approved Seroquel XR for acute treatment of schizophrenia. During its 2007 Q2 earnings conference, AstraZeneca announced plans to launch Seroquel XR in the U.S. during August 2007. However, Seroquel XR has only become available in U.S. pharmacies after the FDA approved Seroquel XR for use as maintenance treatment for schizophrenia, in addition to acute treatment of the illness, on November 16, 2007. The company has not provided a reason for the delay of Seroquel XR's launch.

Health Canada approved sale of Seroquel XR on September 27, 2007.

The FDA approved Seroquel XR for the treatment of bipolar depression and bipolar mania in early October, 2008. According to AstraZeneca, Seroquel XR is "the first medication approved by the FDA for the once-daily acute treatment of both depressive and manic episodes associated with bipolar."

On July 31, 2008, Handa Pharmaceuticals, based in Fremont, California, announced that its abbreviated new drug application (“ANDA”) for quetiapine fumarate extended-release tablets, the generic version of AstraZeneca’s SEROQUEL XR, has been accepted by the FDA.

On December 1, 2008, Biovail announced that the FDA had accepted the company's ANDA to market its own version of sustained-release quetiapine. Biovail's sustained-release tablets will compete with AstraZeneca's Seroquel XR.

On December 24, 2008, AstraZeneca notified shareholders that the FDA had asked for additional information on the company's application to expand the use of sustained-release quetiapine for treatment of depression.

Legal status

Quetiapine received its initial indication from the U.S. Food and Drug Administration for treatment of schizophrenia in 1997. In 2004, it received its second indication for the treatment of mania-associated bipolar disorder. In 2007 and 2008, studies were conducted on quetiapine’s efficacy in treating generalized anxiety disorder and major depression. In April 2009, the Psychopharmacologic Drugs Advisory Committee of the US Food and Drug Administration (FDA) held a public meeting to discuss whether study results supported the FDA's approval for anxiety and depression, with risks of metabolic side-effects and of tardive dyskinesia and sudden cardiac death.

Controversy

AstraZeneca has been sued by the U.S. government over the marketing of quetiapine. A $520 million settlement was reached on October 29, 2009.

Several American soldiers and veterans have died while taking Seroquel for PTSD.

Multiple lawsuits have been filed in relation to quetiapine's side-effects, in particular, diabetes.

Recreational use

Quetiapine is not classified as a controlled substance, "abusive self-administration seems to be driven by quetiapine’s sedative and anxiolytic effects (to help with sleep or to 'calm down') rather than by its antipsychotic properties." Reports of quetiapine abuse have emerged in the medical literature, however, while the drug is usually abused through the crushing and snorting of tablets (insufflation), there have also been reports of intravenous abuse and intravenous co-administration with cocaine. This is commonly referred to as a "Q-Ball". A 2004 letter to the editor of the American Journal of Psychiatry provided an anecdotal estimate that up to 30% of inmates who were seen for psychiatric services in the Los Angeles County Jail were faking psychotic symptoms in an attempt to obtain quetiapine. Also known as "quell", "Snoozeberries", or "Susie-Q", the drug may be more commonly abused in prisons due to its capacity to be regularly prescribed as a sedative and the unavailability in prison of more commonly abused substances. A letter to the editor that appeared in the January 2007 American Journal of Psychiatry has proposed a “need for additional studies to explore the addiction-potential of quetiapine”. The letter reports that its authors are physicians who work in the Ohio correctional system. They report that “prisoners ... have threatened legal action and even suicide when presented with discontinuation of quetiapine” and that they have “not seen similar drug-seeking behavior with other second-generation antipsychotics of comparable efficacy”. It has also been reported that when Seroquel is used with methadone it causes the user to experience a buzz, or opioid euphoria.

References

1. "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
2. Details for Seroquel
3. Patent Document, U.S. Patent and Trademark Office
4. Seroquel patent expiration
5. "Quepin Full Prescribing Information in Drug Reference Encyclopedia". Retrieved 2010-04-03.
6. "quetiapine-fumarate". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
7. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1097/01.jcp.0000248603.76231.b7, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1097/01.jcp.0000248603.76231.b7 instead.
8. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/j.eurpsy.2006.04.007 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/j.eurpsy.2006.04.007 instead.
9. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1089/104454603322572624, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1089/104454603322572624 instead.
10. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1007/s11940-006-0026-6, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1007/s11940-006-0026-6 instead.
11. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1056/NEJMoa051688, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1056/NEJMoa051688 instead.
12. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1136/bmj.38369.459988.8F, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1136/bmj.38369.459988.8F instead.
13. http://www1.astrazeneca-us.com/pi/Seroquel.pdf
14. Shankar Vedantam (2009-03-18). "A Silenced Drug Study Creates An Uproar". The Washington Post.
15. S. Nassir Ghaemi and James Y. Ko (2001). "quetiapine-related tardive dyskinesia". Am J Psychiatry. 158 (10): 1737. doi:10.1176/appi.ajp.158.10.1737. PMID 11579018. {{cite journal}}: Unknown parameter |month= ignored (help)
16. D. Ghelber and R.H. Belmaker (May 1999). "Tardive dyskinesia with quetiapine". Am J Psychiatry. 156 (5): 796–797. PMID 10327920.
17. http://www.tardive-dyskinesia.com/seroquel/
18. Seroquel website
19. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/S0140-6736(09)60742-X, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/S0140-6736(09)60742-X instead.
20. Shibata M, Einhaus S, Schweitzer JB, Zuckerman S, Leffler CW (1993). "Cerebral blood flow decreased by adrenergic stimulation of cerebral vessels in anesthetized newborn pigs with traumatic brain injury". Journal of Neurosurgery. 79 (5): 696–704. PMID 8105043. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
21. ^ Group, BMJ, ed. (2009). "4.2.1". British National Formulary (57 ed.). United Kingdom: Royal Pharmaceutical Society of Great Britain. p. 192. ISBN 0260-535X. Withdrawal of antipsychotic drugs after long-term therapy should always be gradual and closely monitored to avoid the risk of acute withdrawal syndromes or rapid relapse. {{cite book}}: |editor1-last= has generic name (help); Check |isbn= value: length (help); Unknown parameter |month= ignored (help)
22. ^ Kim, DR.; Staab, JP. (2005). "Quetiapine discontinuation syndrome". Am J Psychiatry. 162 (5): 1020. doi:10.1176/appi.ajp.162.5.1020. PMID 15863814. {{cite journal}}: Unknown parameter |month= ignored (help)
23. Michaelides, C.; Thakore-James, M.; Durso, R. (2005). "Reversible withdrawal dyskinesia associated with quetiapine". Mov Disord. 20 (6): 769–70. doi:10.1002/mds.20427. PMID 15747370. {{cite journal}}: Unknown parameter |month= ignored (help)
24. R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1355–1357.
25. AstraZeneca. "Seroquel (quietapine fumarate) tablets" (PDF). 276521. {{cite journal}}: Cite journal requires |journal= (help)
26. Richelson E, Souder T (2000). "Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds". Life Sciences. 68 (1): 29–39. doi:10.1016/S0024-3205(00)00911-5. PMID 11132243. {{cite journal}}: Unknown parameter |month= ignored (help)
27. Davis, Kenneth L; Neuropsychopharmacology, American College of (2002). Neuropsychopharmacology: the fifth ... - Google Books. ISBN 9780781728379.
28. http://www.drugs.com/pro/seroquel.html
29. Kapur, S.; Seeman, P (2001). "Does fast dissociation from the dopamine d(2) receptor explain the action of atypical antipsychotics?:a new hypothesis". American Journal of Psychiatry. 158 (3): 360–369. doi:10.1176/appi.ajp.158.3.360. PMID 11229973.
30. AstraZeneca Pharmaceuticals LP (2011). "SEROQUEL (quetiapine fumarate) tablet, extended release". DailyMed. National Library of Medicine. Section 12.2: Pharmacodynamics. Retrieved 2011-04-26. {{cite web}}: Unknown parameter |month= ignored (help)
31. E. Richelson and T. Souder (November 2000). "Binding of antipsychotic drugs to human brain receptors focus on newer generation compounds". Life Sciences. 68 (1): 29–39. doi:10.1016/S0024-3205(00)00911-5. PMID 11132243.
32. O Gefvert, T Lundberga, I-M Wieselgrenb, M Bergströmc, B Långströmc, F-A Wieselb and L Lindström (April 2001). "D2 and 5HT2A receptor occupancy of different doses of quetiapine in schizophrenia: a PET study". European Neuropsychopharmacology. 11 (2): 105–110. doi:10.1016/S0924-977X(00)00133-4.{{cite journal}}: CS1 maint: multiple names: authors list (link)
33. Oregon State University Drug Use Evaluation: Low-Dose Quetiapine (Seroquel, Seroquel XR) PDF
34. "AstraZeneca Submits an NDA For Sustained Release Formulation Seroquel XR. For the treatment of schizophrenia" (Press release). AstraZeneca. 2006-07-18. Retrieved 2007-01-01.
35. "AstraZeneca Submits EU and Canadian Regulatory Filings for Sustained Release Formulation SEROQUEL XR for the Treatment of Schizophrenia" (Press release). AstraZeneca. 2006-10-19. Retrieved 2007-01-01.
36. "FDA Approves AstraZeneca's Once-Daily SEROQUEL XR Extended-Release Tablets For The Treatment Of Schizophrenia" (Press release). AstraZeneca. 2007-05-18. Retrieved 2007-08-02.
37. "Second Quarter and Half Year Results 2007" (Press release). AstraZeneca. 2007-07-26. Retrieved 2007-08-02.
38. "Seroquel XR Receives Approval from FDA for Maintenance Treatment of Schizophrenia" (Press release). AstraZeneca. 2007-11-16. Retrieved 2007-12-03.
39. Notice of Compliance Information - Seroquel XR September 27, 2007, retrieved December 3, 2007
40. "Biovail Announces Filing of ANDA for Quetiapine XR Tablets" (Press release). Biovail. 2008-12-28.
41. "AstraZeneca Receives FDA Complete Response Letter on Seroquel XR for Major Depressive Disorder" (Press release). AstraZeneca. 2008-12-24. Retrieved 2008-12-28.
42. "QUETIAPINE FUMARATE". Electronic Orange Book. Food and Drug Administration. April 2007. Retrieved 2007-05-24.
43. "AstraZeneca Receives FDA Approval for SEROQUEL in Bipolar Mania" (Press release). AstraZeneca. 2004-01-13.
44. "April 7–8, 2009: Psychopharmacologic Drugs Advisory Committee Meeting Announcement". Retrieved 2009-08-27.
45. Wilson, Duff (2009-10-29). "AstraZeneca Pays Millions to Settle Seroquel Cases". New York Times. Retrieved 2010-03-09.
46. Matthew Perrone (August 30, 2010). "Questions loom over drug given to sleepless vets". Associate Press. Retrieved November 28, 2010.
47. Ann Knef (2007-08-02). "Seroquel suit claims 'so much' is poured into marketing and away from research". The Madison St. Clair Record.
48. Phil Milford (2009-03-11). "AstraZeneca May Link Seroquel, Diabetes, Doctor Says". Bloomberg.com. Bloomberg L.P.
49. http://www.fiercepharma.com/story/astrazeneca-wins-bellwether-seroquel-case/2010-03-19
50. "AstraZeneca pays out million dollar damages". The Local. 2010-08-09.
51. Joseph M. Pierre, M.D., Igor Shnayder, M.D., Donna A. Wirshing, M.D., and William C. Wirshing, M.D. "Intranasal Quetiapine Abuse". American Psychiatric Association.{{cite web}}: CS1 maint: multiple names: authors list (link)
52. ^ Brian M. Waters and Kaustubh G. Joshi (January 2007). "Intravenous Quetiapine-Cocaine Use ("Q-Ball")". Am J Psychiatry. 164 (1). American Psychiatric Association: 173-a-174. doi:10.1176/appi.ajp.164.1.173-a. PMID 17202567. {{cite journal}}: More than one of |work= and |journal= specified (help)
53. Joseph M. Pierre, Igor Shnayder, Donna A. Wirshing, and William Wirshing (September 2004). "Intranasal Quetiapine Abuse". Am J Psychiatry. 161 (9). American Psychiatric Association: 1718. doi:10.1176/appi.ajp.161.9.1718. PMID 15337673. {{cite journal}}: More than one of |work= and |journal= specified (help)CS1 maint: multiple names: authors list (link)
54. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1176/appi.ajp.164.1.174, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1176/appi.ajp.164.1.174 instead.

External links

• "Quetiapine". MedlinePlus. The American Society of Health-System Pharmacists, Inc. 2008-09-01.
• NAMI summary
• Internet Drug List summary
• Compound #1802: Quetiapine ChemBank
• Intranasal Quetiapine Abuse
• U.S. National Library of Medicine: Drug Information Portal - Quetiapine
• Seroquel Adverse Events Reported to the FDA

• Ill-formatted IPAc-en transclusions
• Atypical antipsychotics
• Hypnotics
• Piperazines
• Sedatives
• Dibenzothiazepines
• Ethers
• Alcohols